Water → HCID 59355544, compound
Reaction equation
[NH2:1][C:2]1[C:3](C#N)=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[Cl:8].O.[C:13](=[O:16])(O)[O-:14].[Na+]>S(=O)(=O)(O)O>[NH2:1][C:2]1[C:3]([C:13]([OH:14])=[O:16])=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[Cl:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
3-Amino-4,6-dichloro-pyridine-2-carbonitrile (121 mg) was dissolved in concentrated sulfuric acid (1 mL) and stirred for 1 h at 100° C. The reaction mixture was cooled to room temperature and water (1 mL) was slowly added. The reaction mixture was warmed again to 100° C. and stirred at this temperature for 2 h. Water was added after cooling to room temperature, the pH was adjusted to ˜10 by addition of solid sodium bicarbonate and the aqueous solution was washed 2× with MTB-ether. The aqueous layer was then adjusted to pH ˜2 by addition of 2 M hydrochloric acid and extracted 3× with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuum to afford 99 mg of the title compound of the formula
Workup
- temperatureThe reaction mixture was cooled to room temperature
- temperatureThe reaction mixture was warmed again to 100° C.
- stirringstirred at this temperature for 2 h
- temperatureafter cooling to room temperature
- washthe aqueous solution was washed 2× with MTB-ether
- additionThe aqueous layer was then adjusted to pH ˜2 by addition of 2 M hydrochloric acid
- extractionextracted 3× with ethyl acetate
- washThe combined organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuum
Sources & evidence
- ORD record
- ord-7c387d78d46b4ceb903058081eab7562
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247431B2
Reaction notes
Loading…